2-Benzylidenehydrazono-3-ethoxycarbonylmethyl-1-methoxycarbonylmethylimidazolidin-4-one → 7-Ethoxycarbonylmethyl-1,4,5,7-tetraazabicyclo[4,3,0]-nonan-5-ene-3,8-dione

HRID 1489135Notes

Reaction equation

HRID 1489135 reaction equation
C(=[N:8][N:9]=[C:10]1[N:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13](=[O:21])[CH2:12][N:11]1[CH2:22][C:23]([O:25]C)=O)C1C=CC=CC=1>Cl>[CH2:19]([O:18][C:16]([CH2:15][N:14]1[C:13](=[O:21])[CH2:12][N:11]2[C:10]1=[N:9][NH:8][C:23](=[O:25])[CH2:22]2)=[O:17])[CH3:20]

Participants

3

Reactant 1

HCID 541207212-Benzylidenehydrazono-3-ethoxycarbonylmethyl-1-methoxycarbonylmethylimidazolidin-4-one

Product 1

HCID 229038087-Ethoxycarbonylmethyl-1,4,5,7-tetraazabicyclo[4,3,0]-nonan-5-ene-3,8-dioneYield 39.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 230 mg of the 2-benzylidenehydrazono-3-ethoxycarbonylmethyl-1-methoxycarbonylmethylimidazolidin-4-one obtained in the above Referential Example 2 was added 10 ml of 0.5N hydrochloric acid and the mixture was steam-distilled for 40 minutes. After cooling, the reaction mixture was concentrated under reduced pressure and the residue was charged on silica gel column chromatography, followed by elution with a mixed solvent of chloroform and ethyl acetate (1:2 (v/v)). Thus 60 mg of 7-ethoxycarbonylmethyl-1,4,5,7-tetraazabicyclo[4.3.0]nonan-5-en-3,8-dione was obtained.

Workup

  1. distillationthe mixture was steam-distilled for 40 minutes
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was charged on silica gel column chromatography
  5. washfollowed by elution with a mixed solvent of chloroform and ethyl acetate (1:2 (v/v))

Sources & evidence

ORD record
ord-374be99716834a19b150122937443dd8
Source dataset
uspto-grants-1997_10
Patent number
US05677322

Reaction notes

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